Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-4-trimethylsilanyloxymethyl-tricyclo[9.3.1.0^3,8]pentadec-4-en-2-yl ester

Base Information

• Chemical Name: Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-4-trimethylsilanyloxymethyl-tricyclo[9.3.1.0^3,8]pentadec-4-en-2-yl ester
• CAS No.: 512780-88-0
• Molecular Formula: C₄₃H₆₂O₉Si₂
• Molecular Weight: 779.131

Synonyms:Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-4-trimethylsilanyloxymethyl-tricyclo[9.3.1.0^3,8]pentadec-4-en-2-yl ester

Chemical Property of Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-4-trimethylsilanyloxymethyl-tricyclo[9.3.1.0^3,8]pentadec-4-en-2-yl ester

Chemical Property:

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Technology Process of Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-4-trimethylsilanyloxymethyl-tricyclo[9.3.1.0^3,8]pentadec-4-en-2-yl ester

There total 1 articles about Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-4-trimethylsilanyloxymethyl-tricyclo[9.3.1.0^3,8]pentadec-4-en-2-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + C40H54O9Si (512780-87-9) → Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-4-trimethylsilanyloxymethyl-tricyclo[9.3.1.03,8]pentadec-4-en-2-yl ester (512780-88-0)

Guidance literature:

With 2,6-dimethylpyridine; trifluorormethanesulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at -78 - 0 ℃; for 8h;

DOI:10.1021/jo0206566

Reference yield: 55.0%

Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-4-trimethylsilanyloxymethyl-tricyclo[9.3.1.03,8]pentadec-4-en-2-yl ester (512780-88-0) → Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.03,8]pentadec-4-en-2-yl ester (512780-89-1)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jo0206566

Reference yield:

Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-4-trimethylsilanyloxymethyl-tricyclo[9.3.1.03,8]pentadec-4-en-2-yl ester (512780-88-0) → Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methanesulfonyloxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.03,8]pentadec-4-en-2-yl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 55 percent / CSA / CH₂Cl₂ / 0.5 h / 20 °C

2: 90 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 48 h / 0 °C

3: 72 percent / Cp₂TiCl₂; zinc; ZnCl₂ / tetrahydrofuran / 0.17 h / 25 °C

4: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

With dmap; bis(cyclopentadienyl)titanium dichloride; camphor-10-sulfonic acid; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc(II) chloride; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0206566

upstream raw materials:

trimethylsilyl trifluoromethanesulfonate

C₄₀H₅₄O₉Si

Downstream raw materials:

Benzoic acid (1S,2S,3R,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.0^3,8]pentadec-4-en-2-yl ester

Benzoic acid (1S,2S,3R,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,5-dihydroxy-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-4-methylene-9,14-dioxo-tricyclo[9.3.1.0^3,8]pentadec-2-yl ester

C₄₀H₅₄O₁₀Si

Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,11S)-7-(tert-butyl-dimethyl-silanyloxy)-1,4,5-trihydroxy-4-hydroxymethyl-10-(4-methoxy-benzyloxy)-8,15,15-trimethyl-9,14-dioxo-tricyclo[9.3.1.0^3,8]pentadec-2-yl ester

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